Worth the Risk
by DarylDixon'sgirl1985
Summary: Oliver Wood is bet by two members of the Puddlemore United Quidditch team to date Harry Potter for a year.


**Hey everyone. This story was brought to you by Our Tangled Webs, February Writing Club's Assorted Appreciation, and Yearly Events Thread 2019's Insane Prompt Challenge on Hogwarts School of Witchcraft and Wizardry. For Our Tangled Webs I wrote for the pairing of Oliver/Harry and finished off my first web. For the Assorted Appreciation I wrote for the Ten Things I Hate About You prompt of write the trope the guy dates the girl (or in this case guy) as a bet/dare but fall for her (or in this case him). For The Insane Prompt Challenge I used the prompt #975 which was the title prompt of Worth the Risk. Warning for mentions of sexual preferences and sexual status. I hope you all enjoy the first chapter of Worth the Risk.**

Oliver Wood received multiple slaps on the back from his team mates for making the game winning catch of the Quaffle. Not that he would take all the credit for Puddlemore's win. He couldn't really do that. Harry, who'd agreed to fill in for the Seeker, had been a part of all those wins. He couldn't help but appreciate how much Harry Potter had changed since that first time he saw him on the Quidditch Pitch at Hogwarts.

"I bet you Potter's still a virgin."

This was the statement that broke Oliver at out of his thoughts. He turned to see who was talking about Harry like that finding the team Beaters had been the culprit. Everyone that tall blonde Evan was dating the shorter dark haired Peter. But to hear the two talking so openly about other people like that, in terms of dating and sex, was something Oliver never expected.

"Oliver," Evan called motioning Oliver over to them. "You went to school with Potter. He dates? Right?"

Oliver didn't what Harry Potter did with his free during school. He'd only known the boy for three years back then and the only thing he knew was that Harry only had two friends. Ron and Hermione. Oliver shrugged. "I don't know," he told them causing them to sag in defeat.

"So you wouldn't know if he's like us or if he's..."

Oliver shushed the two as Harry walked towards them. The last thing that Oliver wanted was for Harry Potter to think he was saying lewd things about him. No. That had been Evan and Peter.

"Hey, guys," Harry said. "Good game."

"Sure was," Evan said a look that scared Oliver more than anything coming over his face. It was the wicked smirk he usually got when he was formulating some of idea or another.

"Yeah," Peter said a similar look crossing his face.

Oliver nodded hoping that Harry wouldn't linger longer because you never knew what kind of antics that Evan Peter could get up when they were making their plans. "See you at practice tomorrow," he told Harry.

"Yeah," Harry said waving back as walked out of the changing room.

Oliver let an audible breath he'd been holding without knowing it. But then he turned towards Evan and Peter to be confront with two wicked, evil smirks.

"Were you looking at Potter's butt as he was leaving?" Evan asked.

"I think he was," Peter informed causing a pink blush to crawl up Oliver's face. "Oh, look, Ev, he's blushing."

Oliver felt like smacking himself upside the head for letting himself be caught checking Harry out as the younger man left the changing room. He should have known that Evan and Peter would be watching closely. But then again...

"We kinda guessed you had a thing for Potter," Peter smirked as he and Evan high fived. "It's why you turned down that Bell girl after she asked you out last game to practice with Harry."

"You're being ridiculous," Oliver told them. "I'm just interested in furthering Harry's Quidditch career. That's all."

"Sure," Evan quipped and then it happened. "I bet you woul..."

"He won't take that bet, Ev," Peter stopped the other man. "You heard him. He's just interested in furthering Potter's Quidditch career. Nothing more." He turned to Oliver. "Is that right?"

Oliver nodded.

"Maybe you should have let me finish," Evan groused to Peter playing pushing him. "I was going to say I bet you wouldn't change your mind about the Quidditch career and nothing else thing after a year of dating Harry Potter."

Peter's eyes grew wide as he nodded excitedly. "That's a good one, Ev," he exclaimed. "One year of dating Harry Potter and if you still believe your only interested in him to further his Quidditch career we'll back off. Deal?" He and Evan each held out a hand to seal the deal.

"Deal," Oliver said shaking both hands. He felt a little guilty that he was using Harry for a bet but it really couldn't be help. Now could it? He was about to go change from his Quidditch gear when Evan spoke up again.

"Aren't you going to go ask Harry out?" the blonde asked teasingly.

"Yeah," Peter spoke up. "You should do that before you forget the bet."

Oliver cringed. They were really going to make him do this now. With a sigh he raced out of the changing room to find Harry Potter. He hadn't gone far when he spotted the dark haired bespectacled boy buying coffee from one of the coffee vendors that set up shop during the Quidditch match.

"Harry," Oliver called trying to catch the younger man's attention. He ran over to Harry before the younger man could further. "I was hoping to catch you before you left."

"Well," Harry laughed a sound which was like music to Oliver's ears, "you caught me. What can I do for you?"

Quickly looking around to make sure that no one was listening into their conversation. Oliver mustered up the courage to do what he'd just been bet he couldn't or wouldn't do. "I was wondering if you want to meet up later on tonight for dinner or something like that?" he asked nervously.

"Sure," Harry told him thinking nothing of it. Just two friends meeting up for dinner. "See you later than?"

"Yeah." Oliver watched Harry walk off cursing himself for taking that stupid bet. Then he realized he'd have to make dinner reservations on short notice for the two of them. Running back to the changing room he silently cursed Evan, Peter, and his own stupidity. Could this get any worse? Little did he know he was about to find out.

**I hope you all enjoyed the first chapter of Worth the Risk.**


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